Telling Mom I'm A Crossdresser Part 12: Tow Truck Driver's Big Score

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience.

Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do with the money I am saving I just tell them I am thinking of getting a new car or something, but that’s not the only secret I have. Every Friday, I wear something sexy underneath my clothes and I try to wear something different each time just to be a little naughty while I work. Like last week for example all I wore was a bra some tight panties and stockings or the week before when I wore a baby doll, thong, garter belt and stockings all in white and lace.

This week I decided to put on florescent pink and what better to put on of that color then my pink thong with black lace as well as my garter belt, stockings and corset. I made sure to put on nothing but tight fitting clothes because my uniform for my job was fairly loose fitting which made it perfect to hide different things underneath. Normally days at work are boring and this really brightens up my day, especially when I get home and take off my work clothes and already be dressed. However, today was another boring day where nothing especially exciting happened other then earning my pay and getting my cheque from my boss before I left. This particular day I spent a couple extra hours to help clean up in the kitchen before I left when I realized I was parked in a place that would get me towed if I stayed there over 9:00pm. I had already gotten my money and headed out the door as quick as I could so that I would make sure my car was still where I left it.

When I got to where I parked my car I looked at my watch to see it was 9:05pm. I found a tow truck driver that was just about to hook up my vehicle and drive it away and I immediately tried to get his attention so he would not take off before I got there. The tow truck driver was a fairly well built man. He wasn’t overly big and muscular but he looked to be one of those guys who were slim built but goes to the gym to tone his muscles. The tow truck driver had short hair but it was dark like his gotee and was about the same height as me. At first he looked at me up and down and acted like he was in a rush but when he got a good look at my face he stuttered for a second like he recognized me and introduced himself as Ray.

At first I wondered why his tone seemed to have suddenly changed and then it hit me, the website! I mean it had to have been because I know I have never done any jobs for him before and I have never seen him at the restaurant before. This was an opportunity to use this to try and keep my car and I had to do everything I could because It was mom’s car, not mine and if it got towed my ass would be toast and she would either take it out of my ass or out of Missy’s.

We talked for a while then I asked him in a sweet voice as I smiled if there was anything I could do to keep my car….. and I mean anything. His eyes got as big as watermelons then he looked down at his feet before looking back up and smiling again.

“If Missy comes by my shop at this address in half an hour, I will let her take this car.” He said as he handed me one of his cars that had the address of his shop on it.

I got my bag of emergency Missy items and told him I would be there soon. By this time it was dark so I wasn’t worried too much about walking in the front door as Missy and in such erotic clothing however I didn’t walk the entire distance in my lingerie. I waited till I got to the shop and ducked into an alley. I opened my bag and pulled out my mirror to apply my makeup, then I put on my wig and my fake tits before stuffing my work clothes into the bag. Finally I put on a pair of black 5 inch heels on. I know it didn’t go with my pink theme but it was my emergency bag and they would have to do. I checked to see the coast was clear and made my way to the shop.

I walked in to find it was only Ray that was still there that time of night. I felt relieved yet a little disappointed that it was just the two of us but I didn’t think of it too much because I had to get that car back.

“Hi there, are you Mister Ray? I’m Missy at your service.” I said as I walked up to him then gave a half turn and sat on his counter to cross my legs erotically.

“Yes that’s me and I have to say, you look even more fuck-able in person then you do on your website. I cant wait to shove my cock deep into that ass.” He said with confidence and an obvious bulge in his pants.

He took my bag and put it in the corner of his shop before locking the door and flipping the open sign to closed. Ray grabbed my hand and led me into the main part of his shop where he works. Then Ray got behind me and held my wrists together behind my back and grabbed his duct tape. I gave a little smile as I knew what he was going to do, and I loved it. Ray taped up my wrists, then he put me on my knees and told me if I moved I would be punished severely. I didn’t move as Ray walked away then came back with some rope and a spreader bar. When Ray put the spreader bar on my feet, he gave my ass a little slap and caressed my boy pussy to see how tight I was.

Ray gave a little laugh and complimented on how sexy I looked, and how sexy I would look with his cock up my ass. I blushed and just moaned as he started to tie me up. Nothing too impressive just around my torso between my tits and my elbows but it did add to the excitement.

Once Ray finished tying the knot, he walked around me to admire his handiwork. Once he got in front of me he finally took out his rock hard cock and started stroking it right in front of me.

“Yes! You are definitely going to be a great little fuck toy tonight.” He moaned.

I looked up at him and licked my bright lips and asked for him to fuck me. Ray came closer and pushed his cock into my mouth, fucking it and making me suck him. This continued for a few minutes until my mouth and his cock were all sloppy wet then he pulled away and let me sit there for a second. When Ray came back, he had a hook on a cable that went all the way up to the ceiling which had a pully on it. He attached the hook to the ropes then pulled on the rope until I was on my feet with the spreader bar spreading my legs wide open and my heels making my ass and legs look amazing.

I was now standing and bent over in the only thing I could describe as a bondage version of the standing doggy position and hung up like a piece of meat. It made me horny and feel helpless at the same time and I was getting off on it like a good little slut and ray could tell which made his cock twitch even more.

Ray got behind me and started to rub his cock along the crack of my ass. Then he pulled my thong down to around my thighs so that my asshole could be seen but not my clitty cock. Then he slowly inserted his cock into my ass. It hurt since there was no lube but he was going slow and it still felt good. He went like that for a while and it was feeling a little rough at first but I could feel his cock rub my prostate harder. This felt intense, I have never been fucked without lube before but this was getting me to orgasm faster even though it hurt like my first time again. It wasn’t long before ray needed to cum and he shot his load inside me and I came to. It seemed a little bad that we both came so fast but I knew after all that work it wasn’t going to end there. I told him I had a few things in my bag he could use and he went to get it.

Ray came back in no time at all and he was not only holding the lube I had in my bag but also my lipstick and my butt plug. His cum was starting to drip out of my ass so he coated the plug and my ass in lube then he inserted the plug. I felt so warm now with the cum and lube mixing around my hole then I could feel Ray writing on my body with my lipstick.

I wasn’t able to see what he was writing but I could feel what it was. He wrote “slut” on my lower back just above my ass and “fuck” on my left cheek and “me” on my right one. I moaned in appraise and he smiled before grabbing the plug in my ass, twisting it and shallowly moving it back and forth in my ass. I moaned more and in one quick motion he pulled out the plug. I gave a little yell but Ray slapped my ass then shoved his cock back in. He started to fuck me, harder then before as he thrust hard in and out of me. It was so different then the last fuck he gave me just minutes before but it was great all the same.

“Scream for me you little bitch, beg for my cock and my cum in your ass.” He commanded in that confident yet erotic tone.

This continued for a while and it was about 1am before Ray finally ran out of energy. I guess he has been putting in some long hours and needed to blow off some steam because by the time he was done my stomach was hurting by how full I was and my asshole was sore.

I stuffed my plug back in my ass to hold it in and put my thong back on before going to the bathroom to remove my makeup and wig and put my work clothes back on and trade my heels for my shoes. When I left the bathroom, Ray was waiting for me.

“I had a great time with Missy tonight.” He said with a smile. “I would like to offer her an option. As promised I will not tow her car and as an added bonus I will give it a full detail, tune up, repairs and even a few upgrades as payment for the night. I would also like you to give her this tip. Tell her I said all this was for helping me relax after a long couple weeks of working and letting me live out a little fantasy of mine.” He said as he gave me 200.

I took it and smiled as I said: “I will tell her the message and that is great news thank you so much but how am I going to get home tonight?”

“I will give you a ride home and your vehicle will be ready on Monday. Is that alright?

“Sure, I don’t think My mom or I have any plans for this weekend so I don’t think we will be needing it and if we did I’m sure we could borrow one from a neighbor or something.”

“Alright then, I will take you home.” He said with a smile.

On the way home we just chatted about a few normal things until we got to my driveway. Just as I was getting out he asked for my number in case he wanted to call up Missy again sometime.

I just looked at him and winked as I said: “I think you already know where to find Missy’s number, am I right?”

“Ha ha, yes I suppose I do.” He said with a smile and then drove off and disappeared.

I walked in the door and there was mom asking if she could get something from out of the trunk of the car. I told her it had gotten towed and to say the least she was pissed at first but then told her about the deal I had made with Ray. She suddenly wasn’t angry any more but now looked happy that so much was getting done to the car for free.

“Great! That piece of shit car has been giving me trouble for weeks, now it will run like new. Great work sweetie, but did you have fun?” she asked with a grin like she already knew the answer.

I didn’t say a word as I just turned around and pulled down my pants and my thong to show her my butt plug with cum oozing from the corners and the lipstick markings all over my ass.

Mom got down on her knees and licked some of the cum that was dripping down my thighs then she swallowed and gave a moan like she was saying “delicious”.

Mom just smiled and said “Guess I will have to start wearing lingerie to work as well.”

To be continued.

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